5-Year Startup Student

In early 2009, I finished a prototype to help increase email deliverability. But solving email delivery wasn’t a one-person job. So, I approached Tim Jenkins, one of the smartest people I knew, to join the mission of increasing email deliverability for businesses. Tim joined to be responsible for all backend systems. But, backend systems would be unusable without web applications. So I called on the perfect person for this, Jose Lopez. Once Jose joined, the three of us were ready to begin our journey.

Two years later, in 2011, I went from SendGrid’s CEO, to a role of learning. I call it being a “startup student.” Now, in 2014, at the five-year anniversary of SendGrid, I want to stop to provide my perspective and to share what I have learned.

Luck, Good and Bad

Scaling a company from 3 employees to over 200 (and from 0 to over 250 billion emails) takes luck, culture, and a dedication to rising to challenges. But, most of all it’s about the people.

I will elaborate first on luck. Many things went right for SendGrid to allow us to grow. The market was there when we started—a big factor was the adoption of cloud applications. We crossed paths with awesome executives, investors, and employees who believed in and committed to our mission.

We hired Jim Franklin as CEO in early 2011 and that helped me focus on my software and product passions. Jim established a great culture at SendGrid, the 4Hs (Humble, Honest, Hungry, Happy). Customers had to trust us to solve their email deliverability better than anybody else. Without this trust (that the 4Hs and our focus on culture have allowed us to gain) we never would have started to scale.

We have also experienced bad luck. We have made mistakes in hiring, not adopted processes soon enough, made bad assumptions, got attacked, and had acquisition offers that could have ended SendGrid. What I learned is what you do with those good and bad breaks is what determines the future of the company and what ultimately allows you to scale…or stand still.

Creating Harmony

Maintaining the great culture at SendGrid after five years feels awesome, but it wasn’t an easy feat. I’ve learned that there is a lot of work behind it. Our HR department has a similar task to incorporating musicians in the middle of a symphony. They’ve added key players across the business, while we’ve been at a full sprint, without missing a beat. I’m impressed with their results because people, more than processes are what allow you to scale.

SendGrid has the privilege of being one of the largest email senders in the world. That involves being exposed to unusual problems related to distributed systems, software engineering at scale, and monitoring to react quickly. The synergy between our Ops and Engineering teams keeps 13 billion emails per month flowing smoothly.

Sending many emails on behalf of many customers can only be done right to keep the trust from ISPs. There’s no other option. Our deliverability team has been a great leader for us. Our support team continues to be a great buzz generator by impressing our customers. Investors, customers, and the finance team keep this symphony playing.

But as the company grows, communication gets tougher. With more priorities, comes more noise. So, implementing some processes has been important to allow employees not to think about certain issues and to allow for faster decisions. These decisions have created what SendGrid is today.

What fascinates me is that, no matter what challenges employees face, all 220 employees get up every day to make the email flow, increase email deliverability, and make email better. And they do it with a contagious smile. I am lucky to have the opportunity to learn and work with them. They are who have truly allowed us to scale.